Substituted phenoxypropionates and herbicidal compositions

Abstract

Novel substituted phenoxypropionate of the formula ##STR1## in which R 1 and R 2 each independently are a hydrogen atom or a C 1 to C 6 alkyl group, X is a hydrogen or halogen atom or a nitro, C 1 to C 6 alkyl or C 1 to C 6 alkoxy group, a and n each independently are 1 or 2, and Ar is a group of the formula ##STR2## wherein Y is a trifluoromethyl group, a halogen atom or a nitro, cyano or C 1 to C 6 alkyl group, and b is 1, 2 or 3, and their use as herbicides. Novel intermediates are taught, of the formula ##STR3## in which Z 1 is halogen or a 4-hydroxyphenoxy group.

What is claimed is: 
     
       1. A substituted phenoxypropionate of the formula ##STR94## in which R 1  and R 2  each independently is a hydrogen atom or a C 1  to C 6  alkyl group, X is a hydrogen or halogen atom, a nitro, C 1  to C 6  alkyl or C 1  to C 6  alkoxy group,   a and n each independently is 1 or 2,   Y is a trifluoromethyl group, a halogen atom or a nitro, cyano or C 1  to C 6  alkyl group, and   b is 1, 2 or 3.   
     
     
       2. Compound as claimed in claim 1 wherein R 1  is hydrogen. 
     
     
       3. Compound as claimed in claim 1 wherein R 1  is a C 1  to C 6  alkyl group. 
     
     
       4. Compound as claimed in claim 1 wherein R 2  is hydrogen. 
     
     
       5. Compound as claimed in claim 1 wherein R 2  is a C 1  to C 6  alkyl group. 
     
     
       6. Compound as claimed in claim 1 wherein X is hydrogen, halogen, nitro, C 1  to C 4  alkyl or C 1  to C 4  alkoxy. 
     
     
       7. Compound as claimed in claim 1 wherein a is 1 or 2. 
     
     
       8. Compound as claimed in claim 1 wherein n is 1 or 2. 
     
     
       9. Compound as claimed in claim 1, wherein R 1  and R 2  each independently is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl, X is a hydrogen atom, a fluorine, chlorine, bromine or iodine atom, a nitro, methyl, methoxy, ethyl, ethoxy, n-propyl, n-propoxyl, isopropyl, isopropoxy or n-, iso-, sec- or tert-butyl or -butoxy group, a and n each independently is 1 or 2, Y is a trifluoromethyl group, a fluorine, chlorine, bromine or iodine atom or a nitro, cyano, methyl, ethyl, propyl, isopropyl, n-, iso-, sec- or tert-butyl group and b is 1, 2 or 3. 
     
     
       10. Compound as claimed in claim 1, designated 2-(4-chlorobenzyloxy)-ethyl 2-(4-(4-trifluoromethylphenoxy)phenoxy)-propionate of the formula ##STR95## 
     
     
       11. Compound as claimed in claim 1, designated 2-benzyloxyethyl 2-(4-(4-trifluoromethylphenoxy)-phenoxy)propionate of the formula ##STR96## 
     
     
       12. Compound as claimed in claim 1, designated 3-benzyloxypropyl 2-(4(4-trifluoromethylphenoxy)-phenoxy)propionate of the formula ##STR97## 
     
     
       13. Compound as claimed in claim 1, designated 2-α-methylbenzyloxyethyl 2-(4(4-trifluoromethyl-phenoxy)phenoxy)-propionate of the formula ##STR98## 
     
     
       14. Compound as claimed in claim 1, designated 2-(2-fluorobenzyloxy)-ethyl 2-(4-(4-trifluoromethyl-phenoxy)phenoxy)-propionate of the formula ##STR99## 
     
     
       15. Compound as claimed in claim 1, designated 1-methyl-2-benzyloxyethyl 2-(4-(4-trifluoromethyl-phenoxy)phenoxy)-propionate of the formula ##STR100## 
     
     
       16. A herbicidal composition comprising an agriculturally acceptable carrier and, in herbicidally effective amount, a substituted phenoxypropionate as claimed in claim 1. 
     
     
       17. A herbicidal composition as claimed in claim 30 containing from 0.01 to 95% of the active compound, by weight. 
     
     
       18. A method of combating weeds which comprises applying to the weeds, or their habitat, a herbicidally effective amount of a substituted phenoxypropionate according to claim 1. 
     
     
       19. A method as claimed in claim 18, wherein said compound is applied at a dosage of 0.01 to 2 kg per hectare. 
     
     
       20. A method as claimed in claim 19, wherein said compound is applied at a dosage of 0.05 to 1 kg per hectare. 
     
     
       21. A method as claimed in claim 18, wherein said substituted phenoxypropionate compound is selected from 2-(4-chlorobenzyloxy)ethyl 2-(4-(4-trifluoromethylphenoxy)phenoxy)propionate,   2-benzyloxyethyl 2-(4-(4-trifluoromethylphenoxy)phenoxy)-propionate,   3-benzyloxypropyl 2-(4-(4-trifluoromethylphenoxy)phenoxy)-propionate,   2-α-methylbenzyloxyethyl 2-(4-(4-trifluoromethylphenoxy)phenoxy)-propionate,   2-(2-fluorobenzyloxy)-ethyl 2-(4-(4-trifluoromethylphenoxy)phenoxy)-propionate, and   1-methyl-2-benzyloxyethyl 2-(4-(4-trifluoromethylphenoxy)phenoxy)-propionate.   
     
     
       22. A substituted 2-halogenopropionate of the formula ##STR101## in which R 1  and R 2  each independently is a hydrogen atom or a C 1  to C 6  alkyl group, X is a hydrogen or halogen atom or a nitro, C 1  to C 6  alkyl or C 1  to C 6  alkoxy group,   a and n each independently is 1 or 2, and   Z 1  is a halogen atom or a 4-hydroxyphenoxy group.